Potassium Carbonate → HCID 67110846, compound

HRID 540754Notes

Reaction equation

HRID 540754 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:17][C:16](=[O:27])[NH:15]1)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:12]([N:14]1[C:18]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])=[CH:17][C:16]([O:27][C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[N:15]1)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677672,5-DifluoronitrobenzeneHCID 67111066HCID 67111066, compound

Product 1

HCID 67110846HCID 67110846, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

1,4-difluoro-2-nitrobenzene (0.63 mL, 5.9 mmol, 2.5 equiv) was added to a mixture of 3-(2-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)benzonitrile (500 mg, 2.3 mmol, 1 equiv) and potassium carbonate (970 mg, 7.0 mmol, 3.0 equiv) in dimethyl sulfoxide (5.9 mL). The reaction mixture was heated to 80° C. for 20 minutes, then cooled to 22° C. The crude reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes) to afford 3-[1-ethyl-3-(4-fluoro-2-nitrophenoxy)-1H-pyrazol-5-yl]benzonitrile as light-yellow solid (328 mg, 40%). Calcd (M+1)+: 353.1. Found: 353.0.

Workup

  1. temperaturecooled to 22° C
  2. customThe crude reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe washed solution was dried over sodium sulfate
  6. filtrationThe dried solution was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash-column chromatography on silica gel (hexanes, grading to 50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-8177516df46842a696eb62c1af42c4f1
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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